Facile access to
new one-walled
meso
-substituted
phenylboronic acid-functionalized calix[4]pyrrole (C4P) has been revealed
for the first time, starting from cost-effective and easily accessible
materials. The structures of both the intermediate dipyrromethane
(DPM) and the targeted functionalized C4P have been confirmed by means
of
1
H-NMR,
13
C-NMR, IR, and HRMS spectral data.
The voltammetric investigations of the functionalized C4P films cast
over a glassy carbon electrode (C4P-GCE) clearly establish the redox
stability and redox accessibility of the boronic acid functional moiety
present in the C4P framework. We demonstrate that the presence of
the unique boronic acid functionality in the C4P endows it with an
excellent potential for the highly sensitive electrochemical sensing
of the neurotransmitter dopamine (DA). A linear correlation between
the strength of the Faradaic signals corresponding to the electro-oxidation
of DA over C4P-GCE and the concentration of DA was observed in a concentration
range as wide as 0.165–2.302 μM. The C4P-GCE has revealed
exceptional stability and reproducibility in the electrochemical sensing
of DA, with a nanomolar level limit of detection as low as 15 nM.
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